Tetrahydrofuran → N-[2-(2,5-Dimethylphenoxy)-1-methylethyl]-N-methyl-2-(4-methanesulfonamido-phenyl)-acetamide

HRID 1386476Notes

Reaction equation

HRID 1386476 reaction equation
[CH3:1][NH:2][CH:3]([CH3:14])[CH2:4][O:5][C:6]1[CH:11]=[C:10]([CH3:12])[CH:9]=[CH:8][C:7]=1[CH3:13].O1CCCC1.[CH3:20][S:21]([NH:24][C:25]1[CH:30]=[CH:29][C:28]([CH2:31][C:32]([OH:34])=O)=[CH:27][CH:26]=1)(=[O:23])=[O:22].C1(N=C=NC2CCCCC2)CCCCC1>>[CH3:13][C:7]1[CH:8]=[CH:9][C:10]([CH3:12])=[CH:11][C:6]=1[O:5][CH2:4][CH:3]([N:2]([CH3:1])[C:32](=[O:34])[CH2:31][C:28]1[CH:27]=[CH:26][C:25]([NH:24][S:21]([CH3:20])(=[O:22])=[O:23])=[CH:30][CH:29]=1)[CH3:14]

Participants

5

Reactant 4

HCID 8028TetrahydrofuranHCID 10868DicyclohexylcarbodiimideHCID 2773887{4-[(Methanesulfonyl)amino]phenyl}acetic acidHCID 21182031N-methyl-2-(2,5-dimethylphenoxy)-1-methylethylamine

Product 1

HCID 21182007N-[2-(2,5-Dimethylphenoxy)-1-methylethyl]-N-methyl-2-(4-methanesulfonamido-phenyl)-acetamideYield 70%

Procedure

To a solution containing 0.52 g (2.7 mmol) of N-methyl-2-(2,5-dimethylphenoxy)-1-methylethylamine (Example 45) in 15 ml of tetrahydrofuran 0.63 g (2.7 mmol) of 4-methanesulfonamido-phenylacetic acid (Example 32) and 0.63 g (3.05 mmol) of dicyclohexylcarbodiimide are added and the reaction mixture is stirred at room temperature for 16 hours. After filtration of the mixture, the filtrate is evaporated under reduced pressure and the pale yellowish resin of about 4.5 g obtained is purified by column chromatography by using a mixture of ethyl acetate and hexane as eluent. Thus, 0.76 g (70%) of the title compound is obtained as an amorphous material.

Workup

  1. additionare added
  2. filtrationAfter filtration of the mixture
  3. customthe filtrate is evaporated under reduced pressure
  4. customthe pale yellowish resin of about 4.5 g obtained
  5. customis purified by column chromatography
  6. additiona mixture of ethyl acetate and hexane as eluent

Sources & evidence

ORD record
ord-0e6b9c1f69d14b34ab6a4549f89d3b37
Source dataset
uspto-grants-2001_07
Patent number
US06265445B1

Reaction notes

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